Ammonium Chloride → 6-Iodopyridine-2,3-diamine

To a solution of 5-2 (2.0 g, 7.55 mmol) and NH4Cl (0.202 g, 3.78 mmol) in 2:1 EtOH-H20 (37.8 mL) at 90° C. was added iron powder (2.11 g, 37.8 mmol) in three equal portions over ten minutes. The reaction turned very dark in color. After sixty minutes the hot mixture was filtered through Celite then concentrated. The residue was partitioned between EtOAc and saturated NaHCO3 solution. The organic phase was washed with sat. NaHCO3 solution and brine, then dried with MgSO4 and concentrated to yield a brown solid.

1. filtrationAfter sixty minutes the hot mixture was filtered through Celite
2. concentrationthen concentrated
3. customThe residue was partitioned between EtOAc and saturated NaHCO3 solution
4. washThe organic phase was washed with sat. NaHCO3 solution and brine
5. dry with materialdried with MgSO4
6. concentrationconcentrated
7. customto yield a brown solid

ORD record

ord-0cd9af0083ed425bbb637043bdbb680f

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06693101B2